#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:23:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180260 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/46/7114631.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7114631
loop_
_publ_author_name
'Rong Cai'
'Dawei Wang'
'Yunfeng Chen'
'Wuming Yan'
'Natalie R. Geise'
'Sripadh Sharma'
'Huiyuan Li'
'Jeffrey L. Petersen'
'Minyong Li'
'Xiaodong Shi'
_publ_section_title
;
 Facile synthesis of fluorescent active triazapentalenes through
 gold-catalyzed triazole-alkyne cyclization
;
_journal_name_full               Chem.Commun.
_journal_page_first              7303
_journal_paper_doi               10.1039/C4CC03175J
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C19 H15 N3 O'
_chemical_formula_weight         301.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.8543(7)
_cell_length_b                   18.5471(16)
_cell_length_c                   21.140(2)
_cell_measurement_reflns_used    6049
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.19
_cell_volume                     3079.6(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19159
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0610
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0849P)²+1.5103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1805
_reflns_number_gt                3022
_reflns_number_total             3523
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03175j2.cif
_cod_data_source_block           xs14ccd
_cod_original_cell_volume        3079.5(5)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7114631
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.1513(3) 0.95564(9) 0.72294(8) 0.0766(6) Uani 1 1 d .
N1 N -0.0894(2) 1.07933(8) 0.64657(7) 0.0424(4) Uani 1 1 d .
N2 N 0.0056(2) 1.12519(8) 0.60879(8) 0.0502(4) Uani 1 1 d .
N3 N 0.1349(2) 1.09166(8) 0.57690(8) 0.0518(4) Uani 1 1 d .
C1 C -0.0029(2) 0.87636(9) 0.65389(8) 0.0421(4) Uani 1 1 d .
C2 C -0.0214(3) 0.85323(10) 0.59180(9) 0.0486(4) Uani 1 1 d .
H2 H -0.0711 0.8833 0.5619 0.058 Uiso 1 1 calc R
C3 C 0.0344(3) 0.78532(11) 0.57462(11) 0.0599(5) Uani 1 1 d .
H3 H 0.0199 0.7695 0.5332 0.072 Uiso 1 1 calc R
C4 C 0.1108(3) 0.74115(11) 0.61788(12) 0.0638(6) Uani 1 1 d .
H4 H 0.1505 0.6960 0.6056 0.077 Uiso 1 1 calc R
C5 C 0.1290(3) 0.76346(12) 0.67957(12) 0.0658(6) Uani 1 1 d .
H5 H 0.1809 0.7333 0.7089 0.079 Uiso 1 1 calc R
C6 C 0.0703(3) 0.83071(11) 0.69818(10) 0.0563(5) Uani 1 1 d .
H6 H 0.0800 0.8451 0.7402 0.068 Uiso 1 1 calc R
C7 C -0.0628(3) 0.94937(10) 0.67465(9) 0.0456(4) Uani 1 1 d .
C8 C -0.0132(2) 1.01087(9) 0.63775(8) 0.0381(4) Uani 1 1 d .
C9 C 0.1225(2) 1.02332(9) 0.59574(8) 0.0398(4) Uani 1 1 d .
C10 C 0.2563(2) 0.97225(9) 0.57427(8) 0.0381(4) Uani 1 1 d .
C11 C 0.2763(2) 0.95756(10) 0.51007(9) 0.0457(4) Uani 1 1 d .
H11 H 0.2033 0.9783 0.4806 0.055 Uiso 1 1 calc R
C12 C 0.4056(3) 0.91183(11) 0.49024(10) 0.0530(5) Uani 1 1 d .
H12 H 0.4178 0.9013 0.4475 0.064 Uiso 1 1 calc R
C13 C 0.5155(3) 0.88201(11) 0.53333(10) 0.0531(5) Uani 1 1 d .
H13 H 0.6028 0.8519 0.5197 0.064 Uiso 1 1 calc R
C14 C 0.4969(3) 0.89667(12) 0.59689(10) 0.0534(5) Uani 1 1 d .
H14 H 0.5717 0.8765 0.6260 0.064 Uiso 1 1 calc R
C15 C 0.3668(2) 0.94145(10) 0.61762(9) 0.0458(4) Uani 1 1 d .
H15 H 0.3538 0.9508 0.6606 0.055 Uiso 1 1 calc R
C16 C -0.0567(3) 1.19294(11) 0.61361(11) 0.0586(5) Uani 1 1 d .
H16 H -0.0157 1.2337 0.5931 0.070 Uiso 1 1 calc R
C17 C -0.1903(3) 1.18998(11) 0.65408(11) 0.0567(5) Uani 1 1 d .
H17 H -0.2566 1.2291 0.6664 0.068 Uiso 1 1 calc R
C18 C -0.2124(3) 1.12019(11) 0.67396(9) 0.0498(5) Uani 1 1 d .
C19 C -0.3481(3) 1.08885(16) 0.71635(13) 0.0775(8) Uani 1 1 d .
H19A H -0.4146 1.0546 0.6930 0.116 Uiso 1 1 calc R
H19B H -0.4207 1.1268 0.7314 0.116 Uiso 1 1 calc R
H19C H -0.2954 1.0652 0.7517 0.116 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C18 N1 N2 106.65(15)
C18 N1 C8 149.05(17)
N2 N1 C8 104.30(14)
C16 N2 N3 136.70(17)
C16 N2 N1 109.41(16)
N3 N2 N1 113.89(14)
C9 N3 N2 103.35(15)
C6 C1 C2 119.53(18)
C6 C1 C7 118.93(17)
C2 C1 C7 121.53(17)
C3 C2 C1 119.79(19)
C4 C3 C2 120.6(2)
C3 C4 C5 120.0(2)
C4 C5 C6 120.3(2)
C5 C6 C1 119.7(2)
O1 C7 C8 121.65(17)
O1 C7 C1 120.09(17)
C8 C7 C1 118.25(16)
C9 C8 N1 104.86(14)
C9 C8 C7 132.76(16)
N1 C8 C7 121.75(15)
N3 C9 C8 113.59(15)
N3 C9 C10 117.62(15)
C8 C9 C10 128.64(15)
C15 C10 C11 119.55(17)
C15 C10 C9 120.25(15)
C11 C10 C9 120.14(16)
C12 C11 C10 119.75(18)
C13 C12 C11 120.43(18)
C12 C13 C14 120.05(18)
C13 C14 C15 120.28(19)
C10 C15 C14 119.93(17)
N2 C16 C17 106.86(18)
C16 C17 C18 109.24(18)
N1 C18 C17 107.83(19)
N1 C18 C19 122.74(19)
C17 C18 C19 129.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.240(2)
N1 C18 1.357(2)
N1 N2 1.385(2)
N1 C8 1.416(2)
N2 C16 1.352(2)
N2 N3 1.369(2)
N3 C9 1.332(2)
C1 C6 1.387(3)
C1 C2 1.388(3)
C1 C7 1.499(3)
C2 C3 1.382(3)
C3 C4 1.366(3)
C4 C5 1.376(3)
C5 C6 1.387(3)
C7 C8 1.436(2)
C8 C9 1.407(2)
C9 C10 1.486(2)
C10 C15 1.385(3)
C10 C11 1.393(2)
C11 C12 1.388(3)
C12 C13 1.371(3)
C13 C14 1.379(3)
C14 C15 1.388(3)
C16 C17 1.355(3)
C17 C18 1.372(3)
C18 C19 1.509(3)
